CN114174312A - 空气稳定的Ni(0)-烯烃络合物以及它们作为催化剂或者预催化剂的用途 - Google Patents
空气稳定的Ni(0)-烯烃络合物以及它们作为催化剂或者预催化剂的用途 Download PDFInfo
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- CN114174312A CN114174312A CN202080053726.5A CN202080053726A CN114174312A CN 114174312 A CN114174312 A CN 114174312A CN 202080053726 A CN202080053726 A CN 202080053726A CN 114174312 A CN114174312 A CN 114174312A
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- alkyl
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- same
- cycloalkyl
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- 239000012041 precatalyst Substances 0.000 title claims description 17
- 239000003054 catalyst Substances 0.000 title claims description 14
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 186
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- -1 nickel (II) compound Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
- 229910018597 Ni(BF4)2 Inorganic materials 0.000 claims description 2
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 claims description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 2
- 229910021587 Nickel(II) fluoride Inorganic materials 0.000 claims description 2
- 229910021588 Nickel(II) iodide Inorganic materials 0.000 claims description 2
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 claims description 2
- KVRSDIJOUNNFMZ-UHFFFAOYSA-L nickel(2+);trifluoromethanesulfonate Chemical compound [Ni+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F KVRSDIJOUNNFMZ-UHFFFAOYSA-L 0.000 claims description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(II) nitrate Inorganic materials [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 claims description 2
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 claims description 2
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 35
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
- 239000003446 ligand Substances 0.000 description 29
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 17
- 230000003197 catalytic effect Effects 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000006555 catalytic reaction Methods 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 230000009257 reactivity Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 235000021286 stilbenes Nutrition 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 238000000844 transformation Methods 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000004639 Schlenk technique Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910003074 TiCl4 Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000006254 arylation reaction Methods 0.000 description 4
- 238000006880 cross-coupling reaction Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000004611 spectroscopical analysis Methods 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- RVXPUSSGELSUTI-CLDUCCMASA-N (1e,5e,9e)-cyclododeca-1,5,9-triene;nickel Chemical compound [Ni].C/1C\C=C\CC\C=C\CC\C=C\1 RVXPUSSGELSUTI-CLDUCCMASA-N 0.000 description 3
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 3
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 3
- 238000003430 hydroarylation reaction Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZOLLIQAKMYWTBR-MBKAWSJDSA-N (5e,9e)-cyclododeca-1,5,9-triene Chemical group C1C\C=C\CC\C=C\CCC=C1 ZOLLIQAKMYWTBR-MBKAWSJDSA-N 0.000 description 2
- GTUUHQAAFHVNDC-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-oct-4-en-4-ylbenzene Chemical compound FC1=C(C(=C(C(=C1C(CCC)=CCCC)F)F)F)F GTUUHQAAFHVNDC-UHFFFAOYSA-N 0.000 description 2
- XZDYFCGKKKSOEY-UHFFFAOYSA-N 1,3-bis[2,6-di(propan-2-yl)phenyl]-4,5-dihydro-2h-imidazol-1-ium-2-ide Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1CCN(C=2C(=CC=CC=2C(C)C)C(C)C)[C]1 XZDYFCGKKKSOEY-UHFFFAOYSA-N 0.000 description 2
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- DDEJSGYYURVZHQ-UHFFFAOYSA-N 2-[2-(trifluoromethyl)phenyl]-2H-chromene Chemical compound FC(C1=C(C=CC=C1)C1OC2=CC=CC=C2C=C1)(F)F DDEJSGYYURVZHQ-UHFFFAOYSA-N 0.000 description 2
- LTMBNOZHEBFPMW-UHFFFAOYSA-N 3,4-dipropyl-2-(pyridin-2-ylmethyl)isoquinolin-1-one Chemical compound CCCc1c(CCC)c2ccccc2c(=O)n1Cc1ccccn1 LTMBNOZHEBFPMW-UHFFFAOYSA-N 0.000 description 2
- 238000004679 31P NMR spectroscopy Methods 0.000 description 2
- LMGVDGBKURRIHA-UHFFFAOYSA-N 4,5-dimethyl-2-phenylpyridine Chemical compound C1=C(C)C(C)=CN=C1C1=CC=CC=C1 LMGVDGBKURRIHA-UHFFFAOYSA-N 0.000 description 2
- NWFCNOTUONSUHM-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]morpholine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCOCC1 NWFCNOTUONSUHM-UHFFFAOYSA-N 0.000 description 2
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical class C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
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- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
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Images
Classifications
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- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
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EP19189236.3A EP3771707A1 (en) | 2019-07-30 | 2019-07-30 | Air-stable ni(0)-olefin complex and its use as catalyst and precatalyst |
EP19189236.3 | 2019-07-30 | ||
DE102019214138.2 | 2019-09-17 | ||
DE102019214138 | 2019-09-17 | ||
PCT/EP2020/069898 WO2021018572A1 (en) | 2019-07-30 | 2020-07-14 | Air-stable ni(0)-olefin complexes and their use as catalysts or precatalysts |
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CN202080053726.5A Pending CN114174312A (zh) | 2019-07-30 | 2020-07-14 | 空气稳定的Ni(0)-烯烃络合物以及它们作为催化剂或者预催化剂的用途 |
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US (1) | US20220266232A1 (ja) |
EP (1) | EP3994113B1 (ja) |
JP (1) | JP2022542677A (ja) |
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CN (1) | CN114174312A (ja) |
BR (1) | BR112021026648A2 (ja) |
CA (1) | CA3145230A1 (ja) |
DE (1) | DE202020005813U1 (ja) |
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Citations (3)
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FR1320729A (fr) * | 1959-12-22 | 1963-03-15 | Studiengesellschaft Kohle Mbh | Nouveaux complexes de métaux de transition et procédé pour leur préparation |
US4017526A (en) * | 1959-12-22 | 1977-04-12 | Studiengesellschaft Kohle M.B.H. | Metal complexes |
CN108290829A (zh) * | 2015-12-01 | 2018-07-17 | 科勒研究有限公司 | 用于催化可逆烯烃-腈相互转化的方法 |
-
2020
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- 2020-07-14 EP EP20742680.0A patent/EP3994113B1/en active Active
- 2020-07-14 CN CN202080053726.5A patent/CN114174312A/zh active Pending
- 2020-07-14 KR KR1020227006113A patent/KR20220041864A/ko unknown
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- 2020-07-14 US US17/631,792 patent/US20220266232A1/en active Pending
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2022
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Patent Citations (3)
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FR1320729A (fr) * | 1959-12-22 | 1963-03-15 | Studiengesellschaft Kohle Mbh | Nouveaux complexes de métaux de transition et procédé pour leur préparation |
US4017526A (en) * | 1959-12-22 | 1977-04-12 | Studiengesellschaft Kohle M.B.H. | Metal complexes |
CN108290829A (zh) * | 2015-12-01 | 2018-07-17 | 科勒研究有限公司 | 用于催化可逆烯烃-腈相互转化的方法 |
Non-Patent Citations (2)
Title |
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FISCHER, KARL ET AL.: "The catalytic conversion of olefins, VIII. Naked nickel as a catalyst for the transalkylation of aluminum trialkyls with α-olefins", 《ZEITSCHRIFT FUER NATURFORSCHUNG, TEIL B: ANORGANISCHE CHEMIE, ORGANISCHE CHEMIE》, vol. 39, no. 8, pages 1011 - 1021 * |
LUKAS NATTMANN ET AL.: "An air-stable binary Ni(0)–olefin catalyst", 《NATURE CATALYSIS》, vol. 3, pages 6 - 13, XP093039377, DOI: 10.1038/s41929-019-0392-6 * |
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JP2022542677A (ja) | 2022-10-06 |
US20220266232A1 (en) | 2022-08-25 |
CA3145230A1 (en) | 2021-02-04 |
WO2021018572A1 (en) | 2021-02-04 |
BR112021026648A2 (pt) | 2022-05-10 |
EP3994113B1 (en) | 2024-07-03 |
EP3994113A1 (en) | 2022-05-11 |
DE202020005813U1 (de) | 2022-09-06 |
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